How much does Number 2 complicate the timeline?
Either way, there are contradictions. Pros include the Stark Expo 2010 promo material, the Monaco Grand Prix seen in Iron Man 2 happened in May 2010, and Natasha's line about Bruce going "over a year" without an incident. Some negatives are Fury's "last year" line when referring to Thor's arrival and Darcy's line about Thor being gone "2 Years" in The Dark World (although I guess you can go with her meaning the now 2 years from Thor and The Avengers).
I had earlier discussed how the What-If episode revolving around Fury's Big Week contradicted the old timeline and comic (events that happened on different days in that timeline/comic now happened on the same day and vice versa). As I said that timeline seems obsolete now since it had "I Am Iron Man" 9 months after Tony was captured. The comic also had Fury's Big Week falling a year before The Avengers, but between What-If and now seemingly placing these events in 2010, I wouldn't be surprised if it's at the very least getting ignored and maybe even like the timeline that follows along with it, may be obsolete now.
I hypothetically came up with what Fury's Big Week would now look like following What-If and the new book. This contradicts the comic, but as I said, it seems to be ignored. The specific days of the week come from the What-If episode:
May 30th, 2010 (Sunday)- Tony's Birthday Party. I know his Birthday is the 29th, but What-If tells us the next day is Monday. If it were 2011, the 29th works perfectly as it would be Sunday.
May 31st, 2010 (Monday)- Fury finds Tony at Randy's Donuts, Tony goes through his dad's files, Bruce arrives at Culver University, Tony meets with Pepper in her office, and Coulson leaves for New Mexico. That night, Coulson stops the robbery at the gas station and Thor arrives on Earth. Coulson is wearing the same tie when he's given the detail to watch Tony and when he tells him he's leaving for New Mexico, so for this, all to be the same day isn't too big a stretch.
June 1st, 2010 (Tuesday)- Coulson arrives in New Mexico, Bruce pretends to be a Pizza Delivery driver, Thor tries to steal Mjolnir off the SHIELD base, and back in New York, Tony and Rhodes face off against Vanko at the Stark Expo.
June 2nd, 2010 (Wednesday)- Thor battles against the Destroyer and returns to Asgard, Bruce faces off against Ross at Culver University, and Fury makes Tony a consultant where we can see the news report discussing Culver University.
June 3rd, 2010 (Thursday)- Bruce and Betty hide out at the hotel.
June 4th, 2010 (Friday)- Bruce and Betty travel to New York.
June 5th, 2010 (Saturday)- Bruce and Betty arrive in New York, Harlem Battle.
It'll be interesting to see if Fury's Big Week gets its own section in the book and how it's handled.